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25 September 2018Last updated
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Real Women

Tales of an ex-millionaire

What’s money like in a rich woman’s world? Ashley Waye, 31, tells us what it’s like to fall both in and out of a lot of money, and how she came out the other side

By Ashley Waye
6 May 2015 | 11:45 am
  • Ashley was filthy rich.

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  • Dining out was an every week thing.

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  • Ashley was used to expensive cars.

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  • Dolce & Gabbana.

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  • In her teens Ashley became accustomed to living the high life, eating in upscale restaurants and shopping in designer stores.

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  • Ashley Waye.

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  • The cottage and boathouse in Muskoka, Canada, was the ultimate status symbol.

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  • Ashley is now building a new life with her husband Rob.

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There are a lot of clichés about money. “Money is power”; “Money is the root of all evil”; “Money can’t buy you love”… As someone who has both fallen into a great deal of money, and then fallen out of it again, I can tell you that there is truth in every one of these clichés.

Growing up in Canada, I enjoyed a pretty standard childhood. My father was a businessman and my mother an art historian. We owned our suburban bungalow and I attended a private Montessori school.

When I was six, my dad lost his job, leaving my mother struggling to support the family on her modest income, and requiring me to transfer to state school. But as far as my young mind could tell, things continued as normal. 


Money was power


In fact, I only really became aware of money once we started to have more of it. By 1996, when I was 12, my father was back at work at a software company in Toronto. This resulted in my family’s first windfall: we made our first million dollars. Suddenly we were travelling and I was back at private school. Eventually my father’s work took my family to Berlin in Germany, where he became CEO of a software company. This led to a second windfall, and this time it was big... like, tens of millions big.

It’s fair to say that at this time in my life, I understood we were rich. We lived in the most sought-after area of the city; ate in upscale restaurants daily; owned an expensive car; had in-home massages every week... When we later moved to London, again with my dad’s job, my mum took me to a store called Matches and I discovered Dolce & Gabbana and Chloé. I remember wondering where all this lovely stuff had been all my life! 
I still have the leather pants and suede jacket I purchased on my most memorable shopping spree.

We lived in one of the most exclusive areas of the city, I was at an expensive private school, and my best friend and I would grab taxis on a whim whenever her personal chauffeur was not available to take us to and from school.

The ultimate emblem of our wealth, though, was a gorgeous cottage that my family bought in Muskoka, the most expensive summer resort area in Ontario, Canada. This was a significant status symbol for us, as the area is seen very much as cottage country for the rich (they’re called cottages but really they’re more like mansions).

We had all the bells and whistles in addition to the huge cottage itself – boats, kayaks, canoes and a stunning boathouse with a living space above it that was the size of most apartments in Toronto.


Money was the root of all the evil

The problem with two windfalls in a short period of time is that it creates a false sense of confidence. My father felt invincible and one bad investment led to another and then… Poof!

Just like that, my family’s money was almost gone and there was anger, bitterness, resentment and shame left in its place. After four short years of the good life, at the end of my first year at university in England (an experience that, at about Dh64,400 a year, I would never have been able to enjoy without big money), my father left us.

I was 19 years old and this was the beginning of a very difficult decade of my life; one that would see my whole family mired in litigation; that would see my parents waste every penny they had left on divorce lawyers; that saw so much tension in the family that even my brother and his family were estranged from me for years; that would see me forever estranged from my father; and that would see us lose the cottage, the one place I could call home during my residence in Europe.

After my dad lost a huge chunk of the money, my brother did an accounting of what he had left and explained to him that he would be out of money in four years if he continued to spend at the same rate. I always felt that, as a result of that eye-opener, my dad solved the problem by cutting ties with what he saw as his biggest expense: his family.

However, I don’t blame the money itself – I just feel my father should have been more responsible and careful with our family’s money.

There’s no doubt that having money affected my family though – it meant there was something to fight over (the cottage) for starters. I think when you make money so quickly and lose it so quickly, you get a little desperate and crazy. My father started suing his children to get the cottage back when he realised how much trouble he was in. This friction certainly damaged the family; but again, it was losing the money that caused the stress, not having it! Money solves a lot of problems, but there is no doubt that money can also be partly responsible for a lot of problems too.

Money didn’t buy me love

It surprises me how adaptable we are as human beings: how we can carve out happy moments even during times of loss, how we can adjust to a lavish lifestyle just as quickly as we can learn to accept a tight budget. We are survivors – we have no choice. But that doesn’t mean I don’t sometimes feel resentment. Like when my friends’ parents pay for their weddings, or their deposits on their homes. I do find myself thinking, “That should have been me”. But I also know there is nothing wrong with my friends benefitting from the generosity of their families – if I were in their shoes, I would do nothing differently.

Today, I am fortunate to have met my soulmate, and we are building our financial future from the ground up. I have found my calling as a family lawyer (how ironic!) and have opened my own law firm. My husband and I paid for our own wedding and are now patiently saving for a down payment on a house. We have accepted the possibility that we may have to make plans for children before we become homeowners. My experience has definitely made me very concerned about how I invest and protect my money responsibly once I earn it. 
I still want to enjoy the ‘good life’ – dinners out, treating myself to nice clothing – but it is all in moderation now and I care just as much about planning for my retirement and making sure I don’t end up losing everything on a poor investment decision or on irresponsible spending in general.

It’s definitely not where I thought I would be 15 years ago, but you know what? It’s OK. There is a certain amount of pride that comes with watching my business grow and working with my husband to build a life together. My clients are often coping with losses similar to mine, as money is a major factor in most divorces. In my profession, it is extremely rewarding to be able to draw from my personal experiences to help others navigate the difficult waters of post-separation devastation towards a new chapter of their lives.

I do not regret having and losing. It was having money that gave me access to the rich cultural and academic experiences of my youth; it was losing money that taught me resilience; and both of these shaped who I am today. Money is not the driving purpose of my existence. My loving marriage, my friendships, my family, my work and my compassion for others are what drive me.

Would I like to be rich again? Why not? In the words of Groucho Marx, “Money won’t make you happy, and this is undeniably true, but everything else being equal, it’s a lovely thing to have around the house.”

By Ashley Waye

By Ashley Waye